Waitress to CEO; the untold story of leveraging tips for venture capital
No one I wait on needs to know that serving them the 7th Corpse Reviver #2 of my night isn’t the dream job I had hoped I would have by thirty-three. I do it for the cash, and I make a good amount of it, yet still, I want more.
I am the only person I know who waits tables to fund a startup venture in San Francisco. That line just got me off.
I start my day, usually oversleeping for something…a doctors appointment, an unchartered soul cycle class that’s been on my calendar for a month now, that class pass membership hasn’t seen a return, and I sure as hell am not meditating five minutes every day. I start my mornings usually with the ‘ah, shit, it’s already 9:30' proverbial self-loathing and strong desire to say ‘fuck it’ and go back to bed. ‘Rome wasn’t built in a day, you work hard, you could use 4 more hours of sleep’. But I don’t cater to this success-sucking inner dialogue, NO. Instead, I put the slippers on, the K-cup in the coffee maker, and check my emails. People are already emailing me at 7:30 am, and I am about an hour away from resembling anything close to a human being.
I hear the hiss, splat, and click of the red light going off on Mr. Coffee, and I am off to answer emails, check social media, and push through posts I made the night before.
I have started just about every day like this for the last half a year when I incorporated my side hustle WineUp. You see, I wait tables to pay the bills, and I often work 8 hour shifts until 1 am. And while I am able to make a decent living in the hospitality industry, it is not my passion.
My passion lies in relaying pertinent wine facts to the millennial wine consumer segment in a team-building environment. Full disclosure: I kick ass at it. I get people sounding like wine pros and boosting confidence when describing their taste preferences in under 90 minutes. I find it to be immensley rewarding to run a blind tasting and watch knowledge develop in front of me!
I am obsessed with creating impactful content, marketing, and engaging on social media. What more: all these skills I didn’t know squat about until a few months ago. I taught myself the majority of everything on starting a business through YouTube, asking friends for informational interviews, or making a crap load of mistakes, and learning where I went wrong.
I didn’t know how to drive a Macbook, how to Pin, how to use Google analytics, or even post a blog until 6 months ago — again, all startup tools that were self-taught, and the struggle is still very real.
My day revolves around what seems like a hundred decisions, and actionable steps toward one major goal: get WineUp off the ground so I don’t have to wait tables any more; that is book clients. It’s not that I don’t like being a server, actually, most of the time it’s super fun and comes naturally to me. I even wrote an article about why I am “just a server”, funnily enough I published this a month before I started my business — which goes to show that we are always developing as people.
I do all my own outreach for wine vendor partners, I post on social media 2x minimum a day on IG through feed and multiple story posts, I curate my own content, I write blog posts for my own website, and others’ blogs as well…the list goes on…I engage with people I admire on social media constantly to see how they leveraged their businesses, I tirelessly obsess about diversified revenue streams, I listen to a crap ton of Gary Vee and other podcasts like Millennial Momentum, and How I Built This…I stalk LinkedIn profiles and find out how I can get my next corporate WineUp client, I take people out to drinks, lunch, and “pick their brains”, I schedule IG live wine tastings, I pound the pavement and curate sip & shop nights at retail stores for brand awareness and recognition, I curate wacky food and wine pairings (ask me about Trolli worms and rosé), I make my own newsletter, infographics on Canva and Unfold, and email blasts templates via Mailchimp.
I love every second of building a business: the hustle, the sacrifice, the process, and even waiting tables has started to seem less painful (but if I never have to ask someone how they would like their filet mignon prepared, I will be leaping miles high for joy).
I filed my own LLC, got an EIN, and took out a business banking account. I did that. And…I wait tables full time. I also just started a speaking circuit called “Waitress to CEO; how you can transform your life”, even though I am still waitressing. This is an inspirational talk I have been dreaming of giving for years now, but wasn’t in a place where it made sense. Now it does.
I happen to have a lot to say on the subject of transformation, having made several. I don’t do this because I think it’s going to get me rich and famous (though, that’d be nice), but I genuinely want people to be more “go-gettery” like myself, because #spoileralert: I wasn’t always like this.
The hardest part of my day is the “stop the WineUp founder/CEO job” and take a hurried walk or Lyft ride to my waitress job. Because it’s just me, (but more often than not acting like I have a staffed team), and I am the face, brand, and brainpower behind what is driving WineUp, I have to remain vigilant in my momentum. If I don’t, I will fail. Maybe that’s extreme, but I know I will lose momentum and motivation if I don’t just keep one word in the frontal cortex at all time: Forward.
Every decision I make has to lead me forward.
But, I struggle a lot. I don’t have a ton of patience, or even a modicum of patience — in fact, that is my biggest weakness. I tend to see what I want to be improved first, as opposed to seeing the progress of my personal journey or brand journey. On the other hand, I am grateful that I have become intolerant to bullshit with myself and others because it’s made me strive for success.
I hear sometimes “failure isn’t an option”. Personally, I have learned to accept failure. Failure is the reason I have made big moves, taken leaps of faith, or started something new and wonderful which led to an epic success. For me, all success is, is multiples failures. Make your biggest setback your most inspirational comeback, and it’s like you never failed at all.
Mediocrity, on the other hand scares me, and I just don’t know what to do with it. Mediocrity scares me so much, that I have a spidey sense for it; I can smell it a mile away, and in order to protect myself, I divert in an opposing direction out of fear that it will rub off on me.
I implore more people to stop surfing the wave of mediocrity and getting washed up on the shore of good enough. You’re littering my beach.
Maybe this is a little dramatic, but this is exactly how I feel about Failure vs. Mediocrity. Since I get asked a lot about how I stay motivated, or how I can achieve what I do, or how I create the content in quantities that I do…I decided to carry the proverbial inspiration torch — that is if it will help others understand that personal success it is not about motivation. It is about dedication.
If you are not motivated to change, like I wasn’t for years, then quit your job. Boom…Instantly motivated to seek out a new and better opportunity, right?
If you want to lose weight, but aren’t motivated enough to stick with a diet and exercise plan, then get broken up with. Boom…instant motivation, right? #breakupdiet
My point is: you create your own motivation. Dedication, however, is sticking to your goal by creating impactful habits, which I have found helpful to incorporate things I love into the mix (my favorite part of starting a business is creating content for it, aka writing).
If you don’t love the process, you will not stick to your goal.
I want to be the first successful start-up wine business that was fully funded through tip money. I make a ton of sacrifices to ensure this happens:
- I moved into a less luxurious apartment but that was in closer proximity to all my meetings and WineUp events
- I have said no to parties, trips, and events that I REALLY wanted to go to because I had to wait tables to fund my business and keep me fed
- I had to say “no” to friends that didn’t understand newly arranged priorities, and hence don’t have certain friendships anymore
I have experienced multipled pitfalls along the way:
- I have lost sleep and appetite
- I have gotten unexplained sickness after sickness; strep twice, benign positional vertigo once, two stomach flus, a random kidney infection, and considered hospitalizing myself for depression about two months ago. All the random illnesses started to stop when I moved into a better living situation, so that’s seemingly behind me now.
- It’s not all #femalefounder and #girlboss and millennial pink roses all the time. Life and entreprenuership is DIFFICULT AF.
Quite honestly, sometimes I wish I didn’t stay up until 5 am after 8 hours of waiting tables writing stuff like this. But this is me, this is my cause, this is my call to action: Be more, not less. Be everything you want to be. If you don’t champion for yourself, no one else will.
When I was training for a bodybuilding competition 2 years ago, people would ask me all the time, “how do you stay so motivated”. I thought to myself, ‘because you won’t’.
I want to be a success: the Ted talk, the park bench to Park Place, the state Penn to Penn state type of success story. When I was low, and down, and was collecting car seat change or digging through my trash for receipts to return things I bought so I could pay my rent, these are the kinds of stories that gave me hope. I am a CEO, and I still wait tables to fund my venture. One day I won’t have to, but I write this so I can stay humble when I look back on what it was like while I did.